The first example of enantioselective isocyanosilylation of meso epoxides with TMSCN catalyzed by novel chiral organogallium and indium complexes

被引：47

作者：

Zhu, CJ ^{[1
]}

Yuan, F

Gu, WJ

Pan, Y

机构：

[1] Nanjing Univ, Dept Chem, Nanjing 210093, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 06期

关键词：

D O I：

10.1039/b212511k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The desymmetrization ring opening of meso epoxides using trimethylsilyl cyanide catalyzed by organogallium and indium complexes with binaphthol monoether derivatives as chiral ligands gave beta-isocyanohydrins with moderate to excellent enantioselectivities of up to 95% ee.

引用

页码：692 / 693

页数：2

共 20 条

[1] ASYMMETRIC REDUCTION WITH C-1-SYMMETRIC AND C-2-SYMMETRIC NADH MODEL COMPOUNDS CONTAINING CHIRAL 1,1'-BINAPHTHYLS [J].

AMANO, M ;

WATANABE, M ;

BABA, N ;

ODA, J ;

INOUYE, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (12) :3672-3678

[2] Group 13 compounds incorporating salen ligands [J].

Atwood, DA ;

Harvey, MJ .

CHEMICAL REVIEWS, 2001, 101 (01) :37-52

[3] SYNTHESIS OF ENANTIOPURE N-TERT-BUTOXYCARBONYL-2-AMINOCYCLOALKANONES [J].

AUBE, J ;

WOLFE, MS ;

YANTISS, RK ;

COOK, SM ;

TAKUSAGAWA, F .

SYNTHETIC COMMUNICATIONS, 1992, 22 (20) :3003-3012

[4] Four-coordinate dimethylgallium compounds vary in stability toward hydrolysis [J].

Chesnut, RW ;

Cesati, RR ;

Cutler, CS ;

Pluth, SL ;

Katzenellenbogen, JA .

ORGANOMETALLICS, 1998, 17 (22) :4889-4896

[5] Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides [J].

Cole, BM ;

Shimizu, KD ;

Krueger, CA ;

Harrity, JPA ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1668-1671

[6] Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions [J].

Evans, DA ;

Campos, KR ;

Tedrow, JS ;

Michael, FE ;

Gagné, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7905-7920

[7]

GASMAN PG, 1982, J AM CHEM SOC, V104, P5850

[8] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].

Helmchen, G ;

Pfaltz, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345

[9] Desymmetric ring-opening of meso-epoxides with anilines:: a simple way to chiral β-amino alcohols [J].

Hou, XL ;

Wu, J ;

Dai, LX ;

Xia, LJ ;

Tang, MH .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1747-1752

[10] REACTION OF CYANOTRIMETHYLSILANE WITH OXIRANES - EFFECTS OF CATALYSTS OR MEDIATORS ON REGIOSELECTIVITY AND AMBIDENT CHARACTER [J].

IMI, K ;

YANAGIHARA, N ;

UTIMOTO, K .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1013-1016

← 1 2 →